US3740189A - Black dye formulation containing three mono-azo dyes - Google Patents
Black dye formulation containing three mono-azo dyes Download PDFInfo
- Publication number
- US3740189A US3740189A US00073235A US3740189DA US3740189A US 3740189 A US3740189 A US 3740189A US 00073235 A US00073235 A US 00073235A US 3740189D A US3740189D A US 3740189DA US 3740189 A US3740189 A US 3740189A
- Authority
- US
- United States
- Prior art keywords
- dye
- phenyl
- lower alkyl
- defined above
- black
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/6033—Natural or regenerated cellulose using dispersed dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
- D06P3/8228—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye
- D06P3/8233—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye using dispersed dyes
Definitions
- a black dye formulation comprising a blue dye, an orange or yellow brown dye and a red dye component the dye components being present in proportions suitable for obtaining a black dyestulf which is suitable for application to fibers which will be subjected to durable press treatment, the blue dye component being a compound represented by the formula I wherein X is chlorine, bromine or cyano;
- X is lower alkyl or phenyl
- R is lower alkyl
- R is lower alkyl-or lower alkenyl
- R is hydrogen, lower alkyl or C alkyl substituted by --OCONHR and n is 2 or 3;
- the orange or yellow brown dye component being a compound represented by the formula CHBCHZCN C Hz-R 3 3! wherein X and X are individually chloro or bromo;
- R is Cl-I OCOR -CH OCONHR -CHHCH Cl or C-H-(CH Cl)OCOR R being lower alkyl or phenyl, and R being C -C alkyl, C -C alkenyl or phenyl;
- red dye component being a compound represented by the formula:
- NBC 0X2 wherein X., is H, Cl, Br and ON; X is as defined above; R is as defined above; R is as defined above; it is as defined above.
- the gas exposure test is designed to show the effect of oxides of nitrogen in the atmosphere on the dyestuif.
- One standard fading cycle is established as being approximately equivalent to a six months exposure to the atmosphere in southern New Jersey.
- a dyed fabric withstands 2 cycles of gas exposure, it should show no color change for 12 months under normal wearing conditions.
- Gas fastness is also of importancse in industrial areas with heavy concentrations of fumes or in areas where natural gas is the main fuel used for heating homes.
- the agent which causes gas fading has been identified as nitrogen dioxide.
- the main effect of gas fading is quite often a change in shade.
- the anthraquinone blues are characterized by going redder and duller when gas faded.
- the reaction is nitration, nitrosation, diazotization or oxidation.
- Ozone fading is a pure oxidative reaction. There is very seldom a shade change noted in ozone fading. A loss in depth is the usual manifestation.
- Ozone fading is more prevalent Where there is not a high industrial concentration since in highly industrialized areas the ozone readily reacts with sulfur dioxide, smoke and organic particles in the air since it is a strong oxidizing agent. Ozone fading is intensified in areas where high humidity is dominant.
- the dyestuff is to be applied to a fabric on which a durable press finish is to be superimposed
- the dyestuif must be endowed with the additional attribute of chemical stability and resistance to sublimation. Since durable press finishing is widely practiced in the textile field, especially in connection with polyester-cellulosic fiber blends, and since durable press finishing involves stringent conditions which are very demanding of the dyestuffs applied to the fabric, it is becoming more important with the passage of time to take into consideration the effect of durable press finishing upon the other properties of the dyestu'if.
- Dyestuffs to be used on fabrics which are to receive a durable press finish must be selected on the basis of sublimation fastness and heat stability in order to withstand the high temperatures involved in applying the durable press finish.
- a dyestutf which has sufiicient chemical resistance before being subjected to the high temperatures involvedin durable press finishing, may be unacceptable in the same respect after the durable press finish is applied to the fabric.
- the blue dye component of the black dye formulation of this invention is represented by the following Formula 1:
- Preferred blue dyes are those wherein X is Cl X is lower alkyl R is methyl or ethyl R is methyl or ethyl R is R NHCOO(CH n is 2 or 3.
- the orange or yellow brown dye component of the black dye formulation of this invention is represented by the Formula II:
- R is CH OCOR -CH OCONHR CHOHOH Cl or CH-(CH Cl)OCR R being lower alkyl or phenyl; and R being C -C alkyl, C -C alkenyl or phenyl.
- Preferred orange and yellow brown dyes are those wherein X and X are chloro; and R is CH OCOR wherein R is methyl or ethyl.
- the red dye component of the black dye formulation of this invention is represented by the Formula III:
- R is as defined above; and n is as defined above.
- red monoazo dyestuffs are described in copending application Ser. No. 803,427, referred to above.
- the preferred red dyes for use in the present invention are those wherein X; is Cl; X is lower alkyl; R is CH CH OCONHa1kyl; R is lower alkyl; and n is 2.
- the black dye is formulated by combining the component blue, orange or yellow brown, and red dyes in the following proportions by weight Color: Proportion, parts Blue 50-80 Orange or Yellow Brown 20-50 Red 2-20
- the dye formulation of this invention is suitable for application to many types of synthetic and natural materials, but it is preferred for use in dyeing textile materials, most preferably durable press fabrics, especially those containing cotton and polyester fibers.
- the dyestulf formulations may be applied by wellknown disperse or suspension dyeing techniques from an aqueous dispersion in the presence of a dispensing agent at elevated temperatures.
- the dyestuffs are suitable for application by high temperature dyeing processes, such as are described in US. Pats. 2,415,379, 2,447,993, 2,487,197 and 2,663,612.
- the fabric to be dyed is impregnated at a relatively low temperature with an aqueous dispersion of the dyestuff that advantageously contains 1 to 50% of urea and a thickening agent, such as sodium alginate or, more often, a copolymer derived from acrylic acid.
- the fabric is then squeeze dried in a manner such as to retain over 50% of the dye liquor and the fabric is then heated at a temperature of 375 to 450 F.
- the black dye formulations of the present invention are considered particularly useful for coloring polyester and polyester-cotton blends which are to be treated to impart durable press finish thereto.
- one process involves padding the fabric with a paste comprising 25%' to about 38% of dihydroxydimethylolethyleneurea, a buffered zinc nitrate catalyst, a polyethylene emulsion, a mixture containing nonionic and amphoteric surfactants and an acrylic copolymer emulsion to impart abrasion resistance to the fabric.
- the padded fabric is then dried at 275 F. and cured for 15 minutes at 340 F.
- EXAMPLE 1 A mixture was prepared consisting of: '55 parts by weight of a dispersed paste containing approximately 13% pure dyestuff having the formula:
- the dye formulation was applied by the following thermofixing method: A padding liquor was prepared at a concentration of 16 oz./gal. with the addition of 4.0 oz./gal. of a sodium alginate thickener and 0.2 oz./gal. of a sodium salt of sulfated nonylphenoxy poly(ethyleneoxy) ethanol.
- Polyester-cotton fabric was padded with this liquor at 60 C., dried, and submitted to hot air at 220 C. for 90 seconds.
- the fabric was then padded with 10 oz./gal. sodium sulfide and 5 oz./gal. sodium carbonate (approximately 100% wet pickup), steamed 1 minute at 220 F. and soaped 1 minute at 212 F. with 1 lb./ 100 gal. non-ionic surfactant and 2 lbs./ gal. sodium carbonate. It was thereafter rinsed and dried.
- Both a swatch of fabric treated with the durable press finish and an untreated swatch were characterized by excellent sublimation properties, ozone and gas fastuess. Light and wet-fastness properties were good.
- EXAMPLE 3 This is a comparision of the dyes of Examples 1 and 2 against commercial black dyes.
- Comparative dyeings were made on polyester-cotton swatches in the manner of Example 1 followed by durable press (DP) treatment as described in Example 1.
- An ozone fastness test was made according to the manner of AATCC Test Method 109-1963, Color Fastness to Ozone in the Atmosphere. In these tests 5 shows negligible or no change in color, the lower the number, the greater the color change.
- EXAMPLE 4 The dyestuff mixture of Example 1 was employed to dye polyester-cotton fabric by the thermofixing dyeing method described in Example 1.
- Example 1 was repeated except that the orange component was replaced by the same amount of a dyestuff having the formula:
- a water insoluble black dye formulation comprising a blue dye, an orange or yellow brown dye and a red dye component, the dye components being present in proportions suitable for obtaining a black dyestutf which is suitable for application to fibers which will be subjected to durable press treatment, the blue dye component being a compound represented by the formula 5 I CHzCHzCN wherein X and X are individually chloro or bromo; and R is CH OCOR --CH OCONHR -CHOHCH Cl or -'CH-(CH CI)OCOR R being lower alkyl or phenyl, and R being C -C alkyl, C -C alkenyl or 5 phenyl;
- red dye component being a compound represented by the formula:
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7323570A | 1970-09-17 | 1970-09-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3740189A true US3740189A (en) | 1973-06-19 |
Family
ID=22112560
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00073235A Expired - Lifetime US3740189A (en) | 1970-09-17 | 1970-09-17 | Black dye formulation containing three mono-azo dyes |
Country Status (7)
Country | Link |
---|---|
US (1) | US3740189A (de) |
AU (1) | AU3357471A (de) |
BR (1) | BR7106044D0 (de) |
CA (1) | CA955706A (de) |
CH (2) | CH542315A (de) |
DE (1) | DE2145412A1 (de) |
GB (1) | GB1360048A (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3931145A (en) * | 1972-12-27 | 1976-01-06 | Gaf Corporation | Keto-amido containing phenylazophenyl dyestuffs |
US4083685A (en) * | 1973-06-02 | 1978-04-11 | Bayer Aktiengesellschaft | Process for dyeing synthetic fibre materials from an organic water-immiscible solvent |
US4609727A (en) * | 1981-12-21 | 1986-09-02 | Sandoz Ltd. | 5-C1-4 alkoxy-2-C1-2 alkyl-2',4'-dinitro-6'-halo-4-substituted amino-azobenzenes |
US4826976A (en) * | 1984-09-04 | 1989-05-02 | Polaroid Corporation | Color-shifted dyes with thermally unstable carbamate moiety comprising T-alkoxycarbonyl group |
CN103194091A (zh) * | 2013-04-11 | 2013-07-10 | 沈钢 | 一种高性能多偶氮棕色活性染料及其混合物的合成与应用 |
CN104087008A (zh) * | 2014-07-02 | 2014-10-08 | 绍兴县精细化工有限公司 | 一种分散染料化合物、制备方法及其应用 |
CN104356688A (zh) * | 2014-09-16 | 2015-02-18 | 绍兴县精细化工有限公司 | 一种黄色分散染料组合物及其制备方法和用途 |
CN109517407A (zh) * | 2018-09-30 | 2019-03-26 | 绍兴文理学院 | 一种新型含氨基甲酸酯偶氮分散染料及其制备与用途 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2551432B2 (de) * | 1975-11-15 | 1978-10-19 | Hoechst Ag, 6000 Frankfurt | Verfahren zum Klotzfärben und Bedrucken von Materialien aus gegebenenfalls regenerierter Cellulose und deren Mischungen mit Polyester oder modifizierter Cellulose |
DE2754175A1 (de) * | 1976-12-10 | 1978-06-15 | Ciba Geigy Ag | Verfahren zum faerben oder bedrucken von cellulosehaltigem textilmaterial |
-
1970
- 1970-09-17 US US00073235A patent/US3740189A/en not_active Expired - Lifetime
-
1971
- 1971-09-03 GB GB4120771A patent/GB1360048A/en not_active Expired
- 1971-09-07 CA CA122,176A patent/CA955706A/en not_active Expired
- 1971-09-10 CH CH1328171A patent/CH542315A/de unknown
- 1971-09-10 DE DE19712145412 patent/DE2145412A1/de active Pending
- 1971-09-10 CH CH1328171D patent/CH1328171A4/xx unknown
- 1971-09-15 BR BR006044/71A patent/BR7106044D0/pt unknown
- 1971-09-16 AU AU33574/71A patent/AU3357471A/en not_active Expired
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3931145A (en) * | 1972-12-27 | 1976-01-06 | Gaf Corporation | Keto-amido containing phenylazophenyl dyestuffs |
US4083685A (en) * | 1973-06-02 | 1978-04-11 | Bayer Aktiengesellschaft | Process for dyeing synthetic fibre materials from an organic water-immiscible solvent |
US4609727A (en) * | 1981-12-21 | 1986-09-02 | Sandoz Ltd. | 5-C1-4 alkoxy-2-C1-2 alkyl-2',4'-dinitro-6'-halo-4-substituted amino-azobenzenes |
US4826976A (en) * | 1984-09-04 | 1989-05-02 | Polaroid Corporation | Color-shifted dyes with thermally unstable carbamate moiety comprising T-alkoxycarbonyl group |
CN103194091A (zh) * | 2013-04-11 | 2013-07-10 | 沈钢 | 一种高性能多偶氮棕色活性染料及其混合物的合成与应用 |
CN103194091B (zh) * | 2013-04-11 | 2014-07-23 | 沈钢 | 一种高性能多偶氮棕色活性染料及其混合物的合成与应用 |
CN104087008A (zh) * | 2014-07-02 | 2014-10-08 | 绍兴县精细化工有限公司 | 一种分散染料化合物、制备方法及其应用 |
CN104087008B (zh) * | 2014-07-02 | 2016-04-27 | 绍兴县精细化工有限公司 | 一种分散染料化合物、制备方法及其应用 |
CN104356688A (zh) * | 2014-09-16 | 2015-02-18 | 绍兴县精细化工有限公司 | 一种黄色分散染料组合物及其制备方法和用途 |
CN104356688B (zh) * | 2014-09-16 | 2016-03-23 | 绍兴县精细化工有限公司 | 一种黄色分散染料组合物及其制备方法和用途 |
CN109517407A (zh) * | 2018-09-30 | 2019-03-26 | 绍兴文理学院 | 一种新型含氨基甲酸酯偶氮分散染料及其制备与用途 |
Also Published As
Publication number | Publication date |
---|---|
CH542315A (de) | 1973-05-15 |
GB1360048A (en) | 1974-07-17 |
AU3357471A (en) | 1973-03-22 |
CH1328171A4 (de) | 1973-05-15 |
DE2145412A1 (de) | 1972-03-23 |
BR7106044D0 (pt) | 1973-07-17 |
CA955706A (en) | 1974-10-08 |
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